An efficient solventless synthesis of cycloalkeno-1,2,3-selenadiazoles, their antimicrobial studies, and comparison with parent semicarbazones

Article abstract of DOI:10.1007/s10593-015-1666-9

[Figure not available: see fulltext.] A series of heterocyclic organoselenium compounds, cycloalkeno-1,2,3-selenadiazoles (cyclopenteno, cyclohexeno, cyclohepteno, and cycloocteno-1,2,3-selenadiazoles), was synthesized at room temperature in one step under solventless conditions from the corresponding semicarbazones. The synthesized 1,2,3-selenadiazoles and their parent semicarbazones were screened for their antimicrobial activity against various pathogenic bacteria using agar disc diffusion method. All compounds were found active against E. coli, S. aureus, S. typhi, and P. aeruginosa. Among all the tested selenadiazoles, cyclopenteno-1,2,3-selenadiazole showed excellent inhibition against highly resistant P. aeruginosa. It is observed that selenadiazoles showed higher activity compared with the respective semicarbazones.

Full text of DOI:10.1007/s10593-015-1666-9

DOI 10.1007/s10593-015-1666-9
Chemistry of Heterocyclic Compounds 2015, 51(1), 102–106
An efficient solventless synthesis
of cycloalkeno-1,2,3-selenadiazoles,
their antimicrobial studies,
and comparison with parent semicarbazones
Aditi A. Jadhav1, Vaishali P. Dhanwe1, Prasad G. Joshi1, Pawan K. Khanna1*
1 Nanochemistry Laboratory, Department of Applied Chemistry,
Defence Institute of Advanced Technology (DIAT), Ministry of Defence, DRDO, Govt. of India,
Girinagar, Pune - 411 025, India; e-mail: pawankhanna2002@yahoo.co.in
Submitted November 19, 2014
Accepted December 15, 2014
Published in Khimiya Geterotsiklicheskikh Soedinenii,
2015, 51(1), 102–106
Solventless Synthesis
O
N
SeO2
N
(
)
n
N
N
NH2
(
)
n
Grinding
rt, 15–30 min
H
Se
N
N
N
N
N
N
N
N
Se
Se
Se
Se
n = 1
n = 2
n = 4
n = 3
A series of heterocyclic organoselenium compounds, cycloalkeno-1,2,3-selenadiazoles (cyclopenteno, cyclohexeno, cyclohepteno, and
cycloocteno-1,2,3-selenadiazoles), was synthesized at room temperature in one step under solventless conditions from the corresponding
semicarbazones. The synthesized 1,2,3-selenadiazoles and their parent semicarbazones were screened for their antimicrobial activity
against various pathogenic bacteria using agar disc diffusion method. All compounds were found active against E. coli, S. aureus,
S. typhi, and P. aeruginosa. Among all the tested selenadiazoles, cyclopenteno-1,2,3-selenadiazole showed excellent inhibition against
highly resistant P. aeruginosa. It is observed that selenadiazoles showed higher activity compared with the respective semicarbazones.
Keywords: organoselenium compounds, selenadiazoles, semicarbazones, grinding, solventless synthesis.
tumor activity of benzopyrano-1,2,3-selenadiazole deriva-
tives has been studied against human cell lines, such as
MCF-7, VERO, WI-38, and HEPG-2.12 Activity against
HIV-1 has been reported for 1,2,3-selenadiazole thioacet-
anilides.13 5-Amino[1,2,5]selenadiazolo[3,4-d]pyrimidin-
7-ol has been reported to inhibit cancer cell growth in vitro,
especially that of A375 human melanoma cells.14
Semicarbazones (hydrazine carboxamides), the typical
starting compounds in the synthesis of 1,2,3-selena-
diazoles, are equally interesting for medicinal chemistry.
A literature survey shows that semicarbazones have
potentially broad range of biological applications, e.g.
as anticonvulsant,15 anticancer,16 antioxidant,17 antifungal,18
anti-inflammatory,19 analgesic,20 and antibacterial21
agents.
Organoselenium compounds act as versatile and useful
reagents,1 having interesting chemical reactivity and
potential biological activity.2 Among various types of nitro-
gen- and selenium-containing heterocycles, 1,2,3-selena-
diazoles show interesting reactivity like thermal or
photochemical decomposition resulting in formation of
dimers or in ring opening with extrusion of nitrogen and
elemental selenium leading to acyclic compounds or new
heterocycles.3,4 These properties have allowed to use
1,2,3-selenadiazoles, including cycloalkeno-1,2,3-selena-
diazoles, as important precursors for ligand chemistry5 and
materials chemistry6 including nanotechnology.7 They are
also versatile synthetic intermediates for organic trans-
formations leading to the formation of selenophenes,
alkynes, and 1,4-diselenines.8
In the present study, we present the synthesis and
comparative study of antimicrobial activity of a series of
cycloalkane semicarbazones and the respective cyclo-
alkeno-1,2,3-selenadiazoles. The synthesized compounds
were tested against two Gram-positive and two Gram-
negative bacteria species.
Substituted 1,2,3-selenadiazoles and their derivatives
show antifungal activity.9 1,2-Bis(1,2,3-selenadiazole-4-yl)-
benzene derivatives,10 as well as spiro(chromeno[4,3-d]-
[1,2,3]selenadiazole-4,1'-cyclohexane) derivatives11 have
been reported to possess antimicrobial activity against dif-
ferent Gram-positive and Gram-negative bacteria. Anti-
0009-3122/15/5101-0102©2015 Springer Science+Business Media New York
102

Chemistry of Heterocyclic Compounds 2015, 51(1), 102–106
Scheme 1
O

O
O
N
SeO2
AcONa
N
H2N
( )
n
+
N
N
NH2
(
)
n
.
N
NH2 HCl
( )
n
MeOH
, 5 h
rt, 15–30 min
45–58%
H
Se
H
'
4a–d
1a–d
2
3a–d
1, 3, 4 a n = 1, b n = 2, c n = 3, d n = 4
Synthesis of cycloalkanone semicarbazones and the respective cycloalkeno-1,2,3-selenadiazoles
There are various methods for the synthesis of fused
1,2,3-selenadiazoles and their derivatives from the cor-
responding semicarbazones, including the widely practiced
Lalezari method.22 In all these methods, semicarbazones,
synthesized from various ketones and semicarbazide
hydrochloride, can then be converted to corresponding
1,2,3-selenadiazoles (Scheme 1) via ring closure upon mild
oxidation by selenium dioxide (selenious acid).
One of the remaining problems of the synthesis of
1,2,3-selenadiazoles concerns isolation and purification of
the final products. Thus it is appropriate to offer simpler
alternative methods to get highly purified product within a
short time. Generally, 1,2,3-selenadiazoles are synthesized by
solution chemistry methods using semicarbazones and
SeO2 as starting materials, which implies also longer
reaction times. For example, when 1,4-dioxane is used as a
solvent, the reaction requires 12–24 h of stirring at room
temperature.3,22 Although the use of acetic acid as a solvent
reduces the reaction time, it requires heating of the reaction
mixture at 50–60°C for 2–3 h.8 In refluxing tetrahydrofuran
a similar reaction requires 2–3 h.23 All these solvent-based
methods require heavy work-up. Further, all these methods
require water during work-up to create aqueous and organic
phases for separation of 1,2,3-selenadiazole, which makes
the whole process more complex and affects the final yield
of the product.
To simplify the synthesis and work-up, we herein pre-
sent a solventless method for preparation of cycloalkeno-
1,2,3-selenadiazoles from the corresponding semi-
carbazones, which has not been described previously.
Semicarbazones 3a–d were synthesized by a published
method24 from the respective cycloalkanones 1a–d and
semicarbazide hydrochloride (2).
In contrast to the time- and solvent-consuming solution
chemistry, a solventless cyclization process should be fast
and the isolation of product possible with minimal amount
of solvents. In our experiments, the solventless reaction of
semicarbazones 3a–d with selenium dioxide required hand
grinding only and could be completed within 15–30 min
producing cycloalkeno-1,2,3-selenadiazoles 4a–d3 in
moderate yields.
absorption bands at 2951–2848 cm–1 assigned to C–H
stretching mode of vibrations and at 1648–1627 cm–1
assigned to C=C stretching mode of vibrations. The IR absorp-
tion band at 1482–1436 cm–1 was assigned to C–H defor-
mation mode vibrations, and the band at 1303–1286 cm–1
to C–N stretching mode of vibrations.
–
The 1H NMR spectra of cycloalkeno-1,2,3-selena-
diazoles 4a–d showed different signals for CH2 protons at
α, α', β(β'), and γ(γ') positions in respect to the heterocyclic
ring. Triplet signals at 2.50–3.25 and 2.00–3.15 ppm were
assigned to α- and α'-CH2 groups, respectively, on the basis
of their multiplicity and chemical shift values. Multiplet
signals at 1.50–1.80 and 1.20–1.45 ppm were assigned to
β(β')- and γ(γ')-CH2 groups, respectively, on the basis of
their chemical shifts and number of protons. Similarly, the
13C NMR spectrum of cycloalkeno-1,2,3-selenadiazoles 4a–d
showed the expected number of signals at 150–161, 30–34,
25–27 ppm assigned to C=C, α,α'-CH2, and β,(β',γ, γ')-CH2
carbon atoms, respectively. The proton and carbon chemical
shift values in the NMR spectra of compounds 4a–d
matched well with the reported data.3
Mass spectra of 1,2,3-selenadiazoles showed signals
with a set of isotopic components characteristic of the pre-
sence of selenium which has 8 natural isotopes with atomic
masses 72–82 out of which 6 are stable. The m/z values
corresponded to the corresponding protonated molecular ions.
As of yet, no reports exist on antibacterial studies of
cycloalkeno-1,2,3-selenadiazoles 4a–d to the best of our
knowledge. The activity of synthesized semicarbazones 3a–d
and selenadiazoles 4a–d was tested against some human
pathogenic microbes, two Gram-negative (Escherichia coli,
local resistant Pseudomonas aeruginosa) and two Gram-
positive (Staphylococcus aureus and Salmonella typhi)
species by using agar diffusion method. The agar disc diffusion
method is well documented10,21 and is the standardized method
for determining antimicrobial susceptibility.26
From the results obtained by this method it was found
that some of the tested compounds were highly active even
at concentrations as low as 4.9 mg/ml (Table 1, Fig. 1). For
example, compound 4a showed good inhibition against the
highly resistant Pseudomonas aeruginosa. The extracts of
compounds in dimethyl sulfoxide were active against all
the tested pathogens in a range of inhibition zone diameter
8–25 mm; the solvent DMSO, used also as the control,
showed no activity against any of the tested pathogens.
After initial incubation time of 24 h, antibacterial activities
were determined by measuring zone of inhibition in mm
around each of the disc impregnated with a test compound.
All selenadiazoles 4a–d are active against E. coli,
S. aureus, S. typhi, but compound 4a showed activity also
Although cycloalkanone semicarbazones have been
described earlier,3,25 detailed characterization reports of
these compounds were not found in literature. Therefore,
the structures both of semicarbazones 3a–d and selena-
1
diazoles 4a–d were confirmed by UV-visible, FTIR, H
and 13C NMR spectroscopy and mass spectrometry.
UV-visible spectra of cycloalkeno-1,2,3-selenadiazoles
4a–d showed λmax at ~300 nm of the C=C bond due to π–π*
transition. FTIR spectra of compounds 4a–d showed
103

Chemistry of Heterocyclic Compounds 2015, 51(1), 102–106
Table 1. Sensitivity of human pathogenic microbes
to semicarbazones 3a–d, cycloalkeno-1,2,3-selenadiazoles 4a–d
using the agar disc diffusion method
Zone of inhibition, mm
Com- Concentration,
pound
g/ml
E. coli
9
S. aureus S. typhi P. aeruginosa
0.0049
0.0049
0.0049
0.0049
0.0049
0.0049
0.0049
0.0049
0
8.5
9
7
10.5
11.5
11
11
8
3a
3b
3c
3d
4a
4b
4c
4d
9.2
10
11.5
12
14
0
11
8
18
14
21
25
18.2
15
20
13
Figure 1. Sensitivity of human pathogenic microbes to semicarb-
azones 3a–d and cycloalkeno-1,2,3-selenadiazoles 4a–d using the
agar disc diffusion method.
26
16
0
18
13
0
Experimental
against P. aeruginosa. Additionally, compound 4c was
found highly active against E. coli and S. aureus showing
an inhibition zone of 26 and 25 mm against the respective
bacteria (Table 1). On the basis of the presented data it can
be concluded that the tested 1,2,3-selenadiazoles 4a–d
possess good antimicrobial properties. Similarly, the parent
semicarbazones also showed activity against the four
bacterial species.
UV-visible spectra were recorded at room temperature
qualitatively in the range of 200–800 nm using an Analytik
Jena SPECORD 210 PLUS UV spectrophotometer. FTIR
spectra were recorded at room temperature in neat
substance in the range 4000–800 cm–1 using a FTIR Perkin
Elmer spectrum one spectrometer. 1H and 13C NMR spectra
(300 and 75 MHz, respectively) recorded on a Bruker DRX-
300 instrument in CDCl3, and the chemical shifts were
reported relative to TMS as an internal standard. The high-
resolution mass spectra were recorded on an Agilent
Technologies 6540 UHD Accurate-Mass Q-TOF (LC/MS)
spectrometer with electrospray ionization. Melting points
were determined in open capillaries. The progress of
reactions was monitored by TLC on Merck silica gel 60 F-
254 aluminum sheets, eluent EtOAc, visualization under
UV light. All chemicals and solvents were purchased from
Sigma-Aldrich and Merck India Ltd. All chemicals and
solvents were of reagent or analytical grade and were used
as received.
From the results obtained (Table 1, Fig. 1), it can be
seen that 1,2,3-selenadiazoles 4a–d showed better activity
in comparison to semicarbazones 3a–d, especially against
E. coli, S. aureus, and S. typhi. On the other hand, all four
semicarbazones 3a–d, but only one of the 1,2,3-selena-
diazoles (4a) showed activity against P. aeruginosa. The
differences in the activity between the two series of com-
pounds could be due to the increase in the size of the mole-
cule and changes in the bond angles in the C–N=N–Se–C
fragment upon the formation of the second ring that
influences the bacterial inhibition. The exception in the
case of compound 4a might be due to the small size of its
molecule. The better average antimicrobial activity in
selenadiazoles could be due to the presence of diazole
fragment along with selenium which is a biologically active
element. There are a few selenium-containing organic
compounds in nature with a reported antibacterial activity
which we believe may be due to the presence of selenium
atom, as this is the only bioactive component in their
molecules. Such studies therefore, clearly indicate that
selenium plays an important role for these compounds to
enhance their antimicrobial activity.27
To conclude, we have synthesized a series of cyclo-
alkeno-1,2,3-selenadiazoles from cycloalkanone semi-
carbazones and selenium dioxide using a solventless
method involving grinding of the reactants. Both semi-
carbazones and selenadiazoles were tested for their anti-
microbial activity. The fast and simple method of
formation of such bicyclic organoselenium compounds will
likely promote their application in pharmaceutical chemistry,
biochemistry, microbiology, and nanotechnology. The
selenadiazoles showed enhanced antimicrobial activity
against Gram-positive and Gram-negative bacteria com-
pared with their parent semicarbazones.
Cyclopentanone semicarbazone (3a). In a clean and
dry round-bottom flask, semicarbazide hydrochloride
(15.0 g, 0.135 mol) was suspended in MeOH (125 ml) and
stirred for 5 min at room temperature. Further NaOAc
(14.0 g, 0.170 mol) was added, and the reaction mixture
was refluxed for 2 h. After cooling to room temperature,
the suspension was filtered to obtain free base. The filtrate
was refluxed with cyclopentanone (10.0 g, 0.118 mol) for
3 h. During this time, a white precipitate was formed which
upon cooling was separated by filtration. The progress of
the reaction was monitored by TLC using hexane–AcOEt,
1:1, as solvent system. The product was recrystallized from
EtOH. Yield 17.0 g (75%), white crystals, Rf 0.50, mp 209–
210°C (mp 208–210°C (EtOH)25). UV spectrum (EtOH),
λ
max, nm: 222. IR spectrum, ν, cm–1: 3466 (secondary N–H),
3152 (amide N–H), 1682 (C=O), 1580 (C=N), 1185
1
(NC=O), 2923 (C–H). H NMR spectrum, δ, ppm: 1.55–
1.81 (4H, m, CH2); 2.25–2.51 (4H, m, CH2); 5.81 (2H, br. s,
NH2); 8.70 (1H, s, NH). 13C NMR spectrum, δ, ppm: 18.5
(CH2); 22.1 (CH2); 28.5 (CH2); 38.0 (CH2); 138.0 (C=N);
158.1 (C=O). Found, m/z: 142.0969 [M+H]+. C6H12N3O.
Calculated, m/z: 142.0975.
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Chemistry of Heterocyclic Compounds 2015, 51(1), 102–106
Cyclohexanone semicarbazone (3b) was synthesized
δ), 1296 (C–N s). 1H NMR spectrum, δ, ppm (J, Hz): 3.29
(2H, t, J = 4.8, CH2); 3.01 (2H, t, J = 4.2, CH2); 1.95 (4H,
m, CH2). 13C NMR spectrum, δ, ppm: 25.2 (CH2); 25.3
(CH2); 29.7 (CH2); 33.8 (CH2); 155.6 (C=C); 157.5 (C=C).
Found, m/z: 188.9925 [M+H]+. C6H9N2Se. Calculated, m/z:
188.9926.
analogously to compound 3a from cyclohexanone. Yield
15.8 g (87%), white crystals, Rf 0.55, mp 164–165°C (166–
168°C (EtOH))25. UV spectrum (EtOH), λmax, nm: 265.
IR spectrum, ν, cm–1: 3454 (secondary N–H), 3180 (amide
N–H), 2968 (C–H), 1681 (C=O), 1579 (C=N), 1121
(NC=O). 1H NMR spectrum, δ, ppm: 1.65–1.78 (4H, m,
CH2); 2.14–2.32 (4H, m, CH2); 2.37–2.48 (2H, m, CH2);
6.01 (2H, s, NH2); 7.80 (1H, s, NH). 13C NMR spectrum,
δ, ppm: 26.2 (2CH2); 27.0 (CH2); 28.0 (CH2); 35.1 (CH2);
152.5 (C=N); 158.5 (C=O). Found, m/z: 156.0914 [M+H]+.
C7H14N3O. Calculated, m/z: 156.0931.
Cycloheptanone semicarbazone (3c) was synthesized
analogously to compound 3a from cycloheptanone. Yield
7.50 g (86%), white crystals, Rf 0.60, mp 160–162°C.
UV spectrum (EtOH), λmax, nm: 266. IR spectrum, ν, cm–1:
3462 (secondary N–H), 3144 (amide N–H), 2923 (C–H),
1682 (C=O), 1587 (C=N), 1186 (NC=O). 1H NMR
spectrum, δ, ppm: 1.65–1.85 (4H, m, CH2); 2.21–2.51 (4H,
m, CH2); 2.43 (4H, m, CH2); 6.01 (2H, s, NH2); 7.90 (1H,
s, NH).13C NMR spectrum, δ, ppm: 16.0 (2CH2); 27.1
(2CH2); 33.2 (CH2); 40.1 (CH2); 148.0 (C=N); 159.9
(C=O). Found, m/z: 170.1288 [M]+. C8H15N3O. Calculated,
m/z: 170.1288
Cyclohepteno-1,2,3-selenadiazole (4c) was synthesized
analogously to compound 4a. Yield 3.3 g (55%), yellow
semisolid, Rf 0.70. UV spectrum (PhMe), λmax, nm: 300.
IR spectrum, ν, cm–1: 2919–2848 (C–H), 1649 (C=C), 1440
(C–H δ), 1286 (C–N s). 1H NMR spectrum, δ, ppm (J, Hz):
1.75 (2H, m, CH2); 1.95 (4H, m, CH2); 3.11 (2H, t, J = 5.4,
CH2); 3.37 (2H, t, J = 5.4, CH2). 13C NMR spectrum,
δ, ppm: 26.5 (CH2); 27.0 (CH2); 27.2 (CH2); 29.1 (CH2);
31.3 (CH2); 163.2 (C=C); 160.1 (C=C). Found, m/z:
203.0136 [M+H]+. C7H11N2Se. Calculated, m/z: 203.0082.
Cycloocteno-1,2,3-selenadiazole (4d) was synthesized
analogously to compound 4a. Yield 2.72 g (58%), yellow
liquid, Rf 0.78. UV spectrum (PhMe), λmax, nm: 300.
IR spectrum, ν, cm–1: 2920–2849 (C–H), 1627 (C=C), 1443
(C–H δ), 1303 (C–N s). 1H NMR spectrum, δ ppm (J, Hz):
1.45 (4H, m CH2); 1.89 (4H, m, CH2); 3.16 (2H, t, J = 6.3
CH2); 3.23 (2H, t, J = 6.3, CH2). 13C NMR spectrum,
δ, ppm: 25.2 (CH2); 25.5 (CH2); 26.0 (CH2); 26.5 (CH2);
30.5 (CH2CN); 31.7 (CH2); 159.6 (C=C); 161.5 (C=C).
Found, m/z: 217.0240 [M+H]+. C8H13N2Se. Calculated, m/z:
217.0239.
Antimicrobial study was carried out at Padmaja
Aerobiologicals (P) Ltd. (a Public Testing Laboratory,
FDA Approved, ISO 9001:2008, OHSAS 18001:2007 cer-
tified) at Turbhe, Navi Mumbai, India. Bacterial strains
used in the study were clinical isolates of Staphylococcus
aureus (ATCC 6538), Escherechia coli (ATCC 8739),
Salmonella typhi (NCTC 786), and Pseudomonas aeru-
ginosa (ATCC 9023). Muller–Hinton agar media was used
as a media preparation. For 1000 ml of Muller–Hinton agar
preparation, peptone (5 g), sodium chloride (8 g), beef
infusion (3 g), and agar (16 g) were weighed and dissolved
in distilled water (1000 ml), and maintained at pH 7.3–7.4.
This mixture was sterilized by autoclaving at 121°C for
15 min at pressure 15 psi and used in the tests. All
synthesized compounds 3, 4 a–d were screened for their
antibacterial activity against Gram-positive and Gram-
negative bacteria at concentration 0.0049 g/ml. The
selected bacterial suspension was spread on the surface of
Muller–Hinton agar plates. Whatman no. 1 filter paper
discs (6 mm diameter) were impregnated with 0.0049 g/ml
of DMSO solution of the synthesized compounds. The
discs were placed on solidified media and allowed to
diffuse for 5 min. The agar plates were kept for incubation
of bacteria at 37°C for 24 h. DMSO was used as control. At
the end of incubation, antibacterial activity was determined
by measuring zone of inhibition in mm around each of the
disc.
Cyclooctanone semicarbazone (3d) was synthesized
analogously to compound 3a from cyclooctanone. Yield
14.4 g (92%), white crystals, Rf 0.55, mp 164–165°C.
UV spectrum (EtOH), λmax, nm: 268. IR spectrum, ν, cm–1:
3464 (secondary N–H), 3152 (amide N–H), 1685 (C=O),
1
1580 (C=N), 1180 (NC=O), 2919 (C–H). H NMR
spectrum, δ, ppm: 1.15–1.31 (4H, m, CH2); 1.37–1.48 (4H,
m, CH2); 1.58–1.70 (4H, m, CH2); 2.20–2.45 (2H, m, CH2);
6.20 (2H, s, NH2); 7.81 (1H, s, NH). 13C NMR spectrum,
δ, ppm: 24.0 (2CH2); 25.0 (2CH2); 26.2 (CH2); 28.2 (CH2);
38.0 (CH2); 156.1 (C=N); 158.0 (C=O). Found, m/z:
185.1445 [M+H]+. C9H18N3O. Calculated, m/z: 185.1444.
Cyclopenteno-1,2,3-selenadiazole (4a). Cyclo-
pentanone semicarbazone (3a) (4.2 g, 0.029 mol) and
selenium dioxide (3.3 g, 0.029 mol) were ground together
in a mortar with pestle at room temperature for ca. 20 min.
The process was monitored by TLC using hexane–AcOEt,
7:3, as solvent system. The crude product was dissolved in
PhMe (100 ml) and filtered. The filtrate was evaporated in
rotary vacuum evaporator. The product was purified by
column chromatography on silica gel (60–120 mesh), using
petroleum ether (bp 60–80ºC)–PhMe, 7:3, as eluent.
Viscous (semisolid) reddish product. Yield 1.65 g (45%),
Rf 0.65. UV spectrum (PhMe), λmax, nm: 300. IR spect-
rum, ν, cm–1: 2951–2853 (C–H), 1643 (C=C), 1482 (C–H
δ), 1289 (C–N s). 1H NMR spectrum, δ, ppm (J, Hz): 2.35
(2H, t, J = 4.1, CH2); 1.50 (2H, t, J = 4.1, CH2); 1.21
(2H, m, CH2). 13C NMR spectrum, δ, ppm: 26.3 (CH2);
32.5 (CH2); 34.4 (CH2); 150.6 (C=C); 155.6 (C=C).
Found, m/z: 174.9768 [M+H]+. C5H7N2Se. Calculated, m/z:
174.9769.
Cyclohexeno-1,2,3-selenadiazole (4b) was synthesized
analogously to compound 4a. Yield 3.5 g (58%), yellow
semisolid, Rf 0.72. UV spectrum (PhMe), λmax, nm: 300.
IR spectrum, ν, cm–1: 2931 (C–H), 1648 (C=C), 1436 (C–H
Supporting material to this article containing UV-visible
absorption spectra and IR spectra of compounds 4a–d, as
well as 1H, 13C NMR spectra and mass-spectrum of
compound 4d are available for the authorized users.
105

Chemistry of Heterocyclic Compounds 2015, 51(1), 102–106
9. Jalilian, A. R.; Sattari, S.; Bineshmarvasti, M.; Daneshtalab, M.;
Aditi A. Jadhav thanks Vice Chancellor (DIAT) for
financial support and CDRI, Lucknow for providing NMR
spectra. P. K. Khanna thanks DST, Govt. of India for
research grant through project No. SR/S1/PC-39/2010. We
are thankful to Padmaja Aerobiologicals (P) Ltd., Navi
Mumbai for conducting antibacterial studies. We thank
Dr. Priyesh More for fruitful discussion.
Shafiee, A. Farmaco 2003, 58, 63.
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